


No Regrets, Except Maybe One

by Stephanielikes



Category: Supernatural
Genre: Almost a Novelette, Anal Sex, F/M, Incest, M/M, Oral Sex, Other, SPN Kink Meme, Supernatural Whammy, Switch Dean, Switch Sam, Threesome - F/M/M, Vaginal Sex, Whipping
Language: English
Status: Completed
Published: 2014-10-01
Updated: 2014-10-01
Packaged: 2018-02-19 11:25:26
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 6,579
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2386586
Author URL: https://archiveofourown.org/users/Stephanielikes/pseuds/Stephanielikes
Summary: <blockquote class="userstuff">
              <p>Dean and Sam team up with a hunter they met on a job. Only the boys didn't expect it to go this far.</p>
            </blockquote>





	No Regrets, Except Maybe One

**Author's Note:**

> Dean is 35. Sam is 31. 
> 
> Occurs between 09.14 Captives and 09.15 #thinman.

                Unlocking the door, Dean opened it inwards and held it with one hand, motioning for Astrid to enter first. Her slender thigh brushed his as she shifted her designer duffle bag to fit through. Dean grinned at Sam, cut his brother off and followed their guest into the gaudy motel room. Sam shook his head, bringing up the rear.

                The motel tried to capture the forest cabin feel with whole log veneers on the wall, which clashed with the garish orange shag carpet and drab blue plaid comforters on the two full sized beds. The bedside lamp was covered by a tree-Camo shade which created odd splotches of shadow. The huntress took in the display of newspaper clippings, and photocopied mythology pages taped around the local area map the brothers had hung up on arriving in town.

                “Nice.” Astrid commented in her liquid smoke voice before heading to the breakfast bench in the kitchenette. Her sensible heels clicked on the tiny square of wood laminate. She dropped the tan bag on the seat and opened it. The boys glimpsed the shining of gunmetal and the hard black butt of a machete before she pulled out her own map. Leaving it folded, she dropped the map on the table and unbuttoned her short fitted blazer, slipping it off and draping it over her duffle. She pulled the hem of the maroon satin camisole from her pencil skirt; her bare shoulders glistened in the humidity. The Winchester’s watched in awe as she finally fanned the map out, bending over the table to smooth the far edges. Sam coughed and looked away, smacking Dean’s arm to encourage him to do the same.

                Masquerading as feds had its perks and its pitfalls; the occasional free beer didn’t always make up for having to wear a suit, especially in the cloying August humidity. Dean removed his jacket and tie, and opened up the top buttons on his shirt, then rolled up his sleeves to his elbows. Sam shed his jacket, but only loosened his tie and collar, and untucked the shirt.

                “Fuck me.” Astrid whined turning to face Dean and Sam. Dean bit his tongue to stop from assenting. “Does that thing work or what?”

                Sam blinked; the lace on her blouse clung to the top of her breasts. Sam blinked again and took the few steps to the dirty window air conditioning unit. The boys hadn’t tried it after both examined it and declared it a fire hazard. While that was still true, Sam was willing to risk it for a chance to see the woman’s nipples bud in the artificial chill. He didn’t normally think like that, he told himself as the machine whirred to life and cold air blasted out.

                “It works.” He declared.

                “Thank you, baby Jesus.”

                “Beer?” Dean opened the fridge.

                “Yeah.”

                “Please.”

                Dean handed out uncapped bottles and the three stood considering Astrid’s map.

                “There’s Janet Weatherby. Lindsay Carlson. Erin Appleton.” Astrid pointed to the red marks with this year dated beneath them.

                “This will be Whitney Albrechtsson. Rosana Van Adrichem. Jeanna Mulloy.” Sam followed the system back to the first victim four years ago, but the marks didn’t stop.

                “Who’s this?” Dean tapped the most recent victim that he and Sam didn’t know, noting there was a six year gap between it and Jeanna Mulloy.

                “Max Jones.”

                “Maxine?” Sam went to his laptop on the closest bed and began punching in the name and location.

                “Maxwell.”

                Sam caught Dean’s eye. “So, how long have you been a hunter?” He tried to sound nonchalant. They’d only just met Astrid at the county morgue, asking all the right questions, and looking like sex personified. The corner had answered the inquiries with the sweaty hope his willingness to help would open other avenues.

                Astrid narrowed her slender almond eyes. “A while. Why?”

                “Monsters follow patterns.”

                “I know. That’s how I put together the older victims.”

                “Okay,” Dean spoke up, “but don’t you think switching sides would be a huge change in the pattern?”

                “There could be two.”

                “Like those ghouls?”

                “Or those witches.”

                Sam and Dean bounced the idea around.

                “No. Look.” She touched the corner of Dean’s jaw and turned his head back to the map. “Martin Woodworth, Christiana Kleine, Lisa Condit, Stephen Weddle.” She pointed at each mark, going back fifteen years. “It’s made two changes. It stopped taking male victims and it increased its frequency. Figure out why, and I bet you bag your game.”

                Sam rejoined them at the map propping his left elbow on his right arm and resting his chin on his fist - pondering.

                “Can an incubus even use males, Sammy?”

                Sam rubbed his hand over his cheek. “The lore’s mixed on it. They prefer women at any rate.”

                Dean snickered, “Don’t we all?”

                “Yeah.” Sam and Astrid agreed. There was a stunned silence.

                “Is that really the time?” She grabbed Sam’s wrist and brought the watch face closer. He took his hand back and checked the time against what the bedside alarm clock read, nearly midnight.

                “It’s late.”

                “Do you mind if I borrow a shirt to sleep in? I brought the arsenal, but my clothes are still in my car at the station.”

                “You want to sleep?”

                “It’s not going to attack anyone tonight, right? Not two days after the last.”

                “He’s probably satiated; even the recent victims are months apart.” Sam concurred.

                “Right! I drove all last night and I spent the day trying to get the locals to cooperate. Do you still think it’s the boyfriend? That, um, uh -“

                “Malachi Connell.” Dean provided the name Astrid searched for. “With that name? He’s not fooling anyone. On top of his connections to all six vics.”

                “What about the older ones?” Sam asked returning to his search results.

                “I bet we’d find some.”

                “He was at the same University as Max Jones. 20,000 students and I don’t know if their classes overlapped.”

                “I wager a beer they knew each other well.” Dean grinned goofily.

                “Then we agree and we can sleep?” Astrid’s soft chestnut curls cascaded down her back as she flipped her ponytail off her shoulder. “We can hunt down the demon in his lair tomorrow. He’s apparently attached to the area. I doubt he’ll skip town tonight.”

                Sam dug in his bag for the cleanest, softest flannel he could find before Dean could offer a grungy band shirt. Astrid took Sam’s top with a smile and went into the bathroom. The brother’s watched her flounce away, absently rubbing where she’d touched them.

                “Psst. Sammy.” Dean shucked his shoes. “Fuck off.”

                Sam scowled removing his tie and pulling his shirt over his head. “You fuck off. Aren’t you too old for hook ups?”

                Dean raised his clenched fist; Sam mimicked him. They shook three times and both threw Rock. Sam huffed.

                “Alright if I use a toothbrush?” Astrid leaned out and the boys dropped their arms.

                “Sure.”

                “Thanks!” The door clicked shut and the fists came back.

                Scissors.

                Rock.

                Paper.

                No matter what one picked the other picked the same.

                “We need a vacation from each other.” Sam said when they both held up paper again.

                “You need to respect your elders.”

                Sam wasn’t even thinking about which object to play; he was thinking about the perfectly straight seams running up the back of Astrid’s pantyhose. Not wanting to call attention to his semi hard on, but needing to adjust before the pressure got worse, Sam threw his hands up, as Dean implausibly picked Rock for the fourth time, and spread out on the bed closest to the kitchenette. “You can sleep in the chair.”

                Dean opened and closed his mouth like a suffocating fish. He couldn’t make her sleep in the chair, and he wasn’t quite creepy enough to insist she sleep with one of them. There was no way he was sharing with Sam. The kid flailed and Dean didn’t need to wake with a bony elbow in his ribs. Submitting to his fate, Dean glared and settled in the musty blue recliner.

                Astrid came out wearing Sam’s flannel buttoned only enough to keep it closed, her shoes in one hand and the pile of her clothes in the other, lace bra and thong on top. They watched her deposit the day’s outfit with her other things; leaning to zip the bag, the shirt lifted and the brothers tilted their heads. Dean shifted to make room for his erection. Sam swallowed.

                On the open bed, Astrid sat with one leg folded under her and the other dangling down. Sam envied Dean’s vantage point from the chair; the shirt couldn’t be covering everything. While his own view allowed him a glimpse of the side of her right breast, Dean’s gaze rested low and he licked his lips. Sam reached to turn off the light.

                “You don’t brush your teeth?” Astrid crinkled her nose prettily.

                “Gross, Sam.” Dean hadn’t thought about it either, but was quicker to get up, attempting to shut the door before Sam muscled in.

                They picked up their toothbrushes and tested the bristles for wetness. Both were damp, though neither told the other and each thought theirs was the one thrust into that lush mouth. There was a competitiveness to their brushing, aggressively polishing their pearly whites. Dean finished first filling his mouth with water from the faucet before gargling and spitting, smiling at Sam brightly.

                “Enjoy your alone time.” Dean mimed jerking off as he left Sam glowering and snapped the door shut behind him. Sam heard the light music of Astrid’s laughter and he hastily spit the frothy paste in the sink, following Dean out.

                The woman knelt on the bed, her legs parted and an embarrassed smile spread across her face. Dean inhaled slowly willing his pounding heart to slow. She’d been on her hands and knees, arching her back when he came out of the bathroom. If she had held the pose a second longer, Sam would’ve walked in on Dean forcing himself on her. But she’d laughed, “Pre-bed yoga.”

                Sam took advantage of Dean’s distraction to reinstall himself on the bed. Dean sulked to the chair. Astrid twisted and stretched for the lamp switch. Dean jerked forward in his seat, catching a flash of her bare ass before the room plunged into darkness. She did it on purpose, Dean was sure of it. Every move she made screamed for him. She wanted him and, fuck, he wanted her. He palmed the aching stiffness in his pants believing he did so quietly.

                When Astrid’d turned off the light, her breast slipped out and she’d winked at him. Sam thought of the broad pink areola punctuated by the hard nipple. He bit his lip and pinched his own nipple wondering how well Dean could see in the dark.

                Astrid laid back and smiled, listening to the stifled pants coming from both men. She was playing a dangerous game now. She’d recently lost patience with slowly destroying Mal’s life and decided to just frame him for murder. The faithless bastard gained a reprieve when the two hunters unwittingly stumbled into her sights, smelling irresistibly of whiskey sour testosterone and honey sweet cortisol. She popped the three buttons from their holes and pushed the shirt back bearing her naked flesh to the rising moon, placing bets on who would give in first.

                Convinced he’d waited long enough for everyone else to drift to sleep Dean undid his pants and gripped his cock between thumb and forefinger, curling the others around his balls. He rolled his hips into the sinking realization that it wouldn’t be enough. He gave a few frustrated jerks to be sure.

                Sam pinched his nipple sore before acknowledging the demand in his boxers. As noiselessly as he could, he undid his pants, lifted his hips, and freed his prick. He licked his thumb and rubbed it over his slit. It was okay, but it wasn’t what he wanted. Masturbation lacked the closeness he craved - temporary and fleeting though it might be.

                The heavy weight of Sam Winchester sunk the mattress down. His large rough hand ran over her stomach and grasped her hip, pulling her to him and into a hard kiss. Astrid grinned into it. Dean followed moments after; second only because he’d stripped completely. Dean pushed the back of Sam’s shirt to Astrid’s waist and slid his thick cock between her thighs, the hot head parting her lips as it glided past. She was soaking wet and Dean moaned.

                Astrid broke from Sam’s kiss, sat up, pulling away from Dean too. The brothers’ whines cut short when she removed the shirt and tossed it aside. Sam reached out, but she brushed him away.

                “No clothes allowed.” She commanded laying back and wrapping her arm around Dean as he brought his warm mouth to her breast and suckled the smooth skin. She gave an encouraging gasp.

                Scrambling, Sam shed his remaining clothes. Dean’s hand was buried between her thighs dipping two fingers into her pussy and coating them in slick before sliding back to rub her clit. Sam spread Astrid’s lean legs, lying down with his head between them. He licked the tangy juices from Dean’s fingers sucking the calloused tips and gliding his tongue up their underside. Dean pulled his hand away. He’d seriously been contemplating pushing his dick into Sam’s mouth. Was he really naked and horny in the same bed as his baby brother? Something weird was happening. Dean moved back. Astrid pulled him into a deep kiss. Her tongue thrust into his mouth; his cock throbbed. Losing his train of thought, Dean tugged her close and thrust his hardness into her hip.

                Sam frowned and readjusted kissing her flushed clitoris and lapped between her lips, sinking the stiffened tip of his tongue into Astrid’s soft cunt. Pushing his hands under her hips, he spread her ass. He licked her pussy massaging his thumbs next to her starburst asshole. Shyly he swiped his tongue over the tight ring of muscle. Astrid rewarded him by shoving her fingers through his hair and pulled his face closer.

                Dean grunted rubbing his demanding prick. Repositioning he reached over and picked Astrid up bringing her over his cock. She reached down, lined his pulsing member up, and sank down onto it.

                “Fuck.” Dean moaned penetrating deep.

                Watching with puppy sad eyes as his brother slammed home, Sam licked the slickness on his lips. He’d be hard pressed to describe the flavor, but he was sure it was the best cunt he’d ever tasted.

                Dean thrust slow kissing Astrid’s neck.

                “Let me suck you off, Sam.”

                He had knelt on the bed and was stroking the long length of his cock, but wasted no time, standing up and bringing his prick to her mouth. She smeared the clear bead of pre-come over her pillow soft lips and sucked him down. The way she teased the sensitive spot beneath his crown told a tale of creeping pleasure building until he drained his balls down her throat. Sam wanted to go slow and let her work him with her talented tongue, but his thighs wouldn’t last and neither would his self control.

                Dean pawed her plump breasts, squeezing and circling them beneath his palms. Sam gripped Astrid’s head and plunged his cock in and out; his balls smacked her chin. Her panted breath warmed his flesh. Sam’s thighs started burning from the position. He didn’t want to stop, but he had to slow down. With a little urging from Astrid, Dean gripped Sam’s ass, easing the strain. Sam sighed in relief and bobbed Astrid’s head up and down his dick. She sucked tight and rocked her hips in time with Sam’s thrusts. Dean massaged his brother’s ass as he had Astrid’s breasts. Astrid slid a finger over Sam’s perineum and pressed it dryly into his ass. He gasped and jerked. His insides wound into a tight coil. She wiggled her intruding finger and the coil released. Sam snapped his hips forward filling Astrid’s mouth with sticky come. She waited to swallow until he whimpered from the continued stimulation. He pulled his softening cock out, glistening with spit and semen. Astrid pressed her back against Dean’s chest and looked into his eyes.

                “Lick him.”

                Sam stood straight; the hair on the back of his neck stood on end.

                “Can’t. He’s my…” Dean trailed off. “Sammy.” He breathed in her ear.

                “Sammy would lick you clean. Show him, Sammy. I don’t think he trusts you.”

                Sam kicked Dean’s bowed legs apart and lay down. His brother’s cock continued pumping beautifully into the pink folds of Astrid’s womanhood. Sam rested his forehead on her pelvis and hesitated, inhaling the scent of sex, tired after his orgasm.

                “What’s he-“ Dean gasped as Sam’s pliant tongue caressed the underside of his dick. “Oh.” Dean leaned back picking up his pace. Sammy’s tongue was wet and active, swishing back and forth, rubbing up when Dean was pulled back, laving his testicles when Dean plunged in. “Oh, God, yes.” Dean’s hips stuttered and he grunted coming deep inside Astrid. She picked Sam’s head up off her thigh and rolled off Dean’s twitching cock. A final bubble of come shone in the moonlight that filtered in from the window.

                Astrid pressed her body against Sam’s and nipped his ear as she whispered, “Show him.”

                Sam swallowed Dean’s prick coating it with saliva and licking it clean.

                “Please.” Dean ran his fingers through Sam’s silken hair. “Too much.” He tugged. Sam popped off and kissed Dean’s little belly right below the button.

                The boys dozed, but Astrid was wired. She kissed Dean rubbing her hand over his pulse. Dean felt blood rush south, flushing him hard and poking Sam’s clavicle.

                “Fucking teen.” Sam muttered. Astrid rolled him on his side, kissing him too. Sam kissed back hungrily, his cock taking an interest again.

                “It’s your turn to be middle.”

                Sam nodded and sat up. Dean frowned and Astrid frowned back. If she dosed him more his heart would give out, but he was resisting. She’d been looking forward to two toys all night, but not at the risk of a silver dagger plunged into her own heart. If she had to pick Dean’s ticker or hers, she picked hers.

                Sweet submissive Sammy was on his knees, ass towards Dean, trying to get Astrid’s legs around his waist and his cock in her cunt.

                “Go to my bag and find the lube, baby boy. You deserve it.” Sam went, his pupils blown out.

                In a century or two, Astrid would take the time to analyze the toxins endemic to her species. For now she was happy to use them to get what she wanted. She crawled up Dean’s body and smashed their lips together. Dean kissed back aggressively biting her lip. The succubus massaged her palms over Dean’s pulse points and then licked them for good measure. She started at his temples, then his jaw and neck, the inside of his elbows. She stopped on the way down to his right wrist. That scar. She brushed it with her lips and Dean jerked her head back by her hair. Astrid thought it was over for her, but she laughed anyway with the charge of supernatural energy tingling where she’d touched the mark. Dean forced his tongue into her mouth and Astrid didn’t hold back - she flooded him with her poison. His eyes went glassy and his kiss lost its demand for dominance. He leaned back. A sudden awareness of Sam’s closeness brought Astrid back into focus.

                “On the other bed!” She commanded before he could touch her toxic skin. He looked hurt and confused, but obeyed. “Work yourself loose, angel. Get your ass prepared for Deano’s cock. No less than three fingers. Trust me.” Coating his hand in cool lubrication, Sam lay back. “On your hands and knees. Spread yourself wide. Let us see that pert ass open up.” He rolled onto his stomach and brought his knees up working his fingers into his entrance. “Watch him. Look how he wants you.”

                Dean did watch. Astrid continued her work. Distributing her drugs where the arteries came close to the surface and would deliver the chemicals to all his tissues. She avoided the mark this time. When she made it to the tops of his feet, Dean was chewing his bottom lip and humping the air, his eyes never leaving Sam.

                “Do you want him as much as he wants you?”

                “More.” Dean’s voice was thick with lust.

                “You practically raised him. He should be yours. You deserve him.”

                “No.”

                Astrid’s eyes flashed red, but then she smirked. He wasn’t fighting the effects. He believed he didn’t deserve his brother. She rightly guessed he didn’t just mean like this.

                “Come sit on your brother’s cock, baby.” Astrid beckoned, nearly sure she wouldn’t kill Sam if she touched him now. Sam sighed in relief. His fingers weren’t hitting deep enough, his cock felt neglected and he found it lonely on the other bed despite being three feet from the others. “Have you taken a cock before?”

                “No.”

                “Are you nervous?”

                “No.”

                “Nor should you be. Big bro’s gonna treat you good.”

                Dean gripped the base of his prick and held it steady, petting Sam’s back as Sam straddled him and dropped his rear. Sam gasped and moaned as he took Dean’s dick up his ass. Astrid waited for Sam to grind down to Dean’s hips before she slid him inside of her.

                “Fucking hell.” Sam keened. The creature hid her smile in his collar bone. Rocking forward, Sam plunged deep into the tightness in front of him, and backward, he filled himself with the hardness behind him. Gripping Sam’s hip bones, Dean coached Sam’s sporadic pitch into a fluid undulation. When Sam picked up the rhythm, Dean groped up his little brother’s tight abdomen, higher and higher until he found the delicate nubs and twisted them hard.

                Sam buried his face in Astrid’s neck. “I gotta.”

                “I know.” She purred.

                He wrapped his arms around her back hauling her tight against his chest. Dean took offense to the sudden restriction to his nipple play and pinched with nails. Sam climaxed with a shout. Grunting at the abrupt clench, Dean thrust through it.

                “No more.” Sam begged even as he canted down for Dean.

                “Middles don’t get to stop until everyone’s had their fill.” Astrid scooched back for a better view.

                “Dean.”

                Dean clutched Sam’s shoulders and drove into the slick, tight heat.

                “Come for me.”

                “You want that?”

                “Yes.”

                “Say it.”

                “Come for me?”

                “Tell me what you want me to do.”

                “Blow your load. F-fill me- my ass up.”         

               Her thighs slick with wet and a tacky mixture of Winchester jizz, Astrid rubbed her clit. Sam Winchester awkwardly pleading for an ass full of come was the hottest thing she’d ever seen. It was piss poorly written porno dialogue and she ate it up.

                The boys’ bodies slapped noisily together.

                “Dean.” Sam’s chin lolled to his chest. “Please.”

                “I’m. Gonna. Paint. Your. Insides.” Dean punctuated each word with a jab and ejaculated with a “Bitch.”

                Crumpling to the mattress that barely fit the two men, the pulsing cock slid out of him, and Sam mumbled, “Jerk.”

                She was curious, not stupid, and didn’t call the hunters’ attention to the strange sensations they were experiencing, but, over the lifetimes, Astrid wondered if her toys noticed they were just as driven to fuck but twice as exhausted after each go. Or if they understood she lived off their release. She kissed Sam hard.

                “Shouldn’t Dean be middle now?”

                “Mmm.” Sam agreed meekly though his prick responded as if it were a soldier called to battle, twitching but standing at attention. Astrid reached behind him and smeared her hand in lube and semen, which she used to slick Sam’s cock.

                “Have _you_ taken a cock before, Dean?”

                Silence answered.

                “He’s keeping secrets again, Sammy. How can he expect to be brothers if he can’t be honest with you?” Astrid ran her nails down Sam’s back as she poured polluted words into his ear. “I bet he spreads that sweet pucker for every trucker and burly cop the moment you turn your back. Did you know that?”

                Sam shook his head.

                “How many times have you saved that ass? Dragged his drunken butt back to your safe motel? You deserve the truth.” A nod. “A little thanks.” A nod. “A piece of it.”

                “Yeah.”

                “Has he ever given it to you?”

                “No.”

                “Then take it.”

                A surprised umph was forced from Dean when Sam nearly folded him in half and jabbed his cock against Dean’s taut ass.

                “Make him take it like the dog he is. Blind in his loyalties. Mindlessly obedient. Base.”

                Sam failed to equate his own behavior to her goading. Astrid beamed. Sam flung Dean over and wrenched, tweaked and yanked until a sluggish, befuddled Dean was on his hands and knees. The monster pecked Dean’s cheek and spread her legs in front of him, tapping her mons in lieu of a verbal command. Dipping his face into her loins, Dean began to lick her clean from ass to clitoris. Sam fondled Dean’s raised haunches casting around the room in search of some item. Astrid watched closely, she didn’t expect to have to give him a booster, though who knew what manner of taint flowed through his veins, but Sam returned with one of their black leather belts. The succubus’ taunts couldn’t have been more successful. Sam questioned her with a look.

                “He deserves no better.”

                Doubled up, the belt strap cracked sharply. A piece of Dean wanted to run, but the rest agreed and braced for the first strike.

                “Don’t stop or I’ll have him go twice as long as he intends.” Astrid scolded the hunter back to caressing her pussy. Sam whipped the thong flat into the back of Dean’s thighs. The whimper vibrated prettily through Astrid’s cunt as Dean kept licking. Two more blows landed in quick succession; angry welts rose where they connected. Sam smiled, letting his improvised whip slip in his grip.

                “You barely stung him.”

                Sam frowned at the pulsing red stings, but took up his scourge and struck twice more.

                “Didn’t even stop eating me out.”

                The belt whistled through the air before biting into Dean’s backside. He whimpered and sucked Astrid’s clit. Sam scowled lashing Dean’s ass until Dean was bleating in pain, and a thin line of blood welled up from the split flesh, but Dean dived right back into Astrid’s cunt after every blow. Frustrated, Sam threw the belt against the wall. Dean flinched. Astrid pulled his head into her, cutting off his air. Sam shoved his aching prick balls deep into Dean’s ass in one thrust. Dean’s tongue finally stilled when he screamed. Nails dug into his side.

                “Sammy?” Dean quailed.

                “Shut up, slut.” Sam snarled, pointedly ratcheting his hips. Astrid moaned, as close to an orgasm as she’d ever been. Sam jack-hammered without mercy, impaling his brother on his dick. Laying at Dean’s side, Astrid wrapped her hand around his leaking prick, jerking him to completion while she rubbed herself.

                “Shit!” Sam sunk in as Dean’s muscles pulsed with his release. Ramped up, Sam slammed hard enough to slide Dean into the headboard. The younger grabbed it for leverage, fucking hard as the older gurgled and choked on unshed tears. Sam came pumping his brother’s ass full of his hot seed. He bit Dean’s shoulder, bruising it and nearly breaking the skin before he went limp sending them flat to the mattress; his dick softened inside Dean.

                Astrid guided Sam to the other bed for a rest, smirking at the sticky red line across his lap. Pushing Dean onto his back, she kissed him and felt him grow stiff. She sucked his left nipple to a wet peak and blew cool air over it. Dean’s breath hitched and he gyrated against her ass. The succubus teased his length with her wet lips, rubbing her sex slowly up his shaft. Dean came as quick as an adolescent and dry.

                “You really are not living up to any of your reputations.” Astrid wiggled until his soft cock was inside her. He hissed, trying to push her off. Another kiss, another erection swelled and stretched her pussy wide. She adored the feeling of a dick growing hard in her cunt. She squeezed him pulsing her muscles. He held out for nearly a minute before rutting up into her for a quarter minute more and whimpered through another orgasm. Continuing to grind on Dean, the creature palmed her perky, round breast, throwing her head back and looking at the other Winchester. He was struggling to stay awake, watching her fuck his brother, his cock at half mast.

                “Come here.” She panted. “I want to teach you something special.”

                Sam’s feet dragged through the carpet as he hauled himself up on Astrid’s command. She met him at the edge of the bed, coaxing him between his brother’s bowed legs, rubbing her palm over his temple and through his hair. She pressed her lips against his left eyelid.

                “Put his ankles on your shoulders. Good. Now take one finger and feel the top of his channel until you reach the little bundle.” Sam obeyed and Dean’s hips jerked. “Excellent. Get a good feel for where it is.” Sam gauged the depth with his finger and probed the spot, noting the difference between it and the surrounding organ. “Now do it again, but use your penis.”

                Sam penetrated his brother a second time, gentler, his coerced fury lost to exhaustion. Besides tilting his hips to allow Sam’s crown to massage his prostate, Dean didn’t participate, not even when Sam pushed a thumb into his mouth. They fucked sweetly for near twenty minutes before Dean peaked, a dribble of jizz smearing across his belly. Sam stopped thrusting. He couldn’t just pull out and lay down. He wanted to, but he needed to come more than he needed to breathe.

                “What’s the matter, baby boy? Don’t you want it?”

                “Not gonna hurt him.”

                Astrid stopped herself from adding ‘again’ for Sam. “Use his mouth.”

                Sam groaned with unwanted desire. Gliding his cock over that broad, silken tongue sounded better than a thousand years in Heaven. Astrid proped Dean’s head with a pillow and parted his lips with her sex soaked fingers.

                “In you go.”

                Scrambling up the body beneath him, Sam nudged the tip close. Teeth scraped his sensitive skin as he eased into the readied mouth. Dean’s shallow breathing circulated warm and cool air around Sam’s shaft. He halted when his brother’s throat squeezed and Dean gagged on his girth. With a confused urge to come quickly, but make it last as long as possible, Sam jerkily plunged in and out of the wet heat surrounding his dick.

                While Sam fucked his face, Astrid ran her hands up Dean’s calves, but paid close attention to Sam. When he was at the tipping point, his hips stuttering and ass clenching, she said, “come on his face.”

                The younger Winchester popped out of the older’s cracked and bruised mouth, jacking off until pearly strings of semen splattered over Dean’s pretty features and into his hair. Sammy collapsed, the effort required to keep breathing was all he could muster. Astrid picked him up and dumped him on the second bed.

                The night was winding down; the boys had a round or two each left in them. Two-thirds drained they became as exciting as dildos - pleasurable in their own right, but frustrating that one had to do all the work. Astrid planted a kiss on Dean’s femoral pulse and sucked on the resulting hard on. Shining him with her saliva and then inhaling the energy as he came hard, though dry, with a plaintive wheeze of pain.

                “Me.” Sam managed, struggling. The succubus whipped her face to him, in the moonlight, her gorgeous angular features distorted in a flash into something livid and monstrous.

                “What?” Her voice was venom. He shouldn’t be coherent enough to talk, let alone demand.

                “Take. Me.” He couldn’t see if Dean was still breathing, or if his intervention had been an orgasm too late. Fighting against exhaustion and the drug haze, Sam rolled onto his back, shallow ineffective breaths segmenting his speech. “Leave. My - Dean. Be.”

                Astrid sauntered to Sam Winchester’s side. She told herself to be angry, never before had anyone been so hard to get and keep under, but she smiled. The challenge was more thrilling than the sex. She kissed the big, dumb man and he whimpered as his dick hardened for her. She straddled him, bouncing on his balls like a peppy cheerleader.

                “Oh, Sammy.” She sighed. “So sweet. So giving.” He held her hips, trying to rally as though if he fucked her hard enough she would move on. Astrid nipped his ear lobe whispering, “I’ll take you both.”

                Sam fainted when he came.

                Climbing off, Astrid stood between the beds and observed the naked, vulnerable men, deathly pale and clinging to lives that were - by all accounts - shit. Was it kinder to put them out of their misery? She pondered. Sam was done now or dead after the next, but whatever that mark on Dean was interfered with her instincts. She screwed the older brother again and, when his heart didn’t give out, she fucked him a final time out of pure amazement.

                As satisfied as she had been in ages, Astrid dug to the bottom of her bag and removed two black butt plugs, one a bit larger than the other - parting gifts for the night’s entertainment. The succubus made no effort to find the bottle of lubrication, rolling Sam onto his stomach and working the smaller toy into his tight little rosebud. Hours had passed since Dean had banged his baby brother, but traces of slick and semen remained. When she pushed Dean over, the cherry red blisters were too tempting to ignore, and she collected the belt to add a dozen of her own weeping lacerations before she shoved the larger plug into his asshole.

                Thinking about how she’d like to do them again in a decade or two when their guards were down, or sooner if they were idiotic enough to come after her, Astrid showered, dressed, jotted a message on the hanging map and left with her bag.

 

                When he first came around, the warm, damp cloth scrubbing his face was soothing like a mother’s touch, but it kept coming back and Dean thought of course he’d get stuck with Mrs. Bates. He intended to tell off whoever was rubbing the top layer of his skin raw, but barely managed to make a hum in discomfort.

                “I know, but it’s already dried.” Sam responded, his voice hoarse and weak. “Can you drink?”

                Only one of Dean’s eyes opened, something glued the lashes of his other closed. He knew what and he wished he didn’t. He remembered more of last night than he would ever admit.

                “Eh.” Not a word, but better than a minute earlier.

                Water sloshed when Sammy dropped the washcloth in the filled ice bucket. Unscrewing the cap of a silver flask he pressed the lip into Dean’s mouth and tipped out a swallows worth. The liquid burned going down, but lacked flavor.

                Dean coughed.

                “Holy water.” Sam said, his head beginning to droop and he took a sip too. Wringing out the cloth, he pressed it over Dean’s stuck eye. “Let it soak.” Sam lay down. “Just need a minute.”

 

                Sam woke. It was night again. He felt Dean’s neck for a pulse; his brother twitched and grumbled. Sam fell back asleep.

                Morning sun spilled into the room; Dean’s hand was tugging between his buttocks and he was whimpering. His fingers were too clumsy to get a grip to pull the flared bulb out. The jostling stirred Sam. Noticing Dean’s struggle, guilt twisted his stomach. The first time he got up and could move, he’d pulled the sex toy from his ass while squatting on the toilet. He then laid in the bottom of the tub focusing on breathing and staying awake while the hot shower turned cold. Accidentally grabbing the flask of Holy water instead of whiskey, he’d discovered, though it wasn’t a proper antidote, it eased the pressure in his chest and it stopped his heart from feeling as if it were making a jail break. Sam’d then rested before gathering what he could to clean up Dean. Bile burned his throat at the thought of examining what he’d done to Dean’s rear end. He’d given in to the Siren’s call of sleep without even finishing cleaning his come from his brother’s face.

                Sam slapped Dean’s hand away.

                “Out.” Dean complained.

                “I got it.” Sam grasped the flanged end. “On three. One. Two.” Sam yanked the plug out. Dean groaned biting back a wail.

                “Fucker.”

                “You started it.” Sam tossed the toy on the floor.

 

                The crackle of a police scanner and the smell of coffee woke Dean up. He couldn’t remember putting on the clean boxers he was wearing and he wasn’t half as tacky and gross as he should’ve been. Sam sat clothed and fresh from a shower on the other bed. As Dean tested his range of motion, the pull of adhesive bandages on his buttocks and the pain inside his ass stopped him. After a few deep breaths and knowing what to expect, he mustered the strength and grimaced through, delicately sitting with his back on the headboard, arms folded over his chest and eyes closed.

                “Nothing looked infected.” Sam spoke to the coffee cup he held on his knee. “There was blood but I couldn’t tell if it was from the - or my… I should take you to the hospital just in case.”

                “I’m fine.”

                Sam sighed. He hadn’t the energy to drag Dean to the car or he would’ve done it while Dean was unconscious. He was astonished Dean hadn’t banned talking as soon as he could. Then he realized his brother probably felt as numb as he did, and his third thought was that was a sign of psychological trauma, and the Winchesters had a blanket ban on talking about mental issues.

                The scanner hissed and the dispatcher blandly called the code for a domestic disturbance. Sam clicked it off.

                “They found Connell yesterday with his heart ripped out.”

                “How long ago was she here?”

                “Three days.”

                Dean’s eyes snapped open. Three days lost and probably another four just to recover enough to get back to the bunker. He’d been sitting for only a few minutes and he was on the verge of giving up and lying on his side. He looked at Sammy, who resolutely kept his eyes averted and appeared sick but uninjured. Dean noticed it when glancing around the room. Something had been added to their map in orange sharpie. He stood.

                “Dean. You’ve got to rest.” Sam grabbed his shoulder, but Dean shook him off and shuffled closer.

                “Did you see this?”

                “What?” Sam held Dean’s elbow in an offer of physical support.

                Two X’s overlapped each other, marked about where their motel was, were annotated with the year, and beneath that, in a loopy feminine hand, the bitch had scrawled:

_Thanks That was fun!_

**Author's Note:**

> Written as a fill for the SPN Kink Meme prompt (http://spnkink-meme.livejournal.com/88207.html?thread=34639503#t34639503): Sam and Dean (with no previous sexual relationship) get whammied by a succubus/some kind of lady sex monster, and are filled with the irresistible need to fuck her. Neither has the self-control to take turns, so they end up in a threesome with progressively increasing incestuousness, while the succubus is encouraging them to touch each other and having the time of her life.


End file.
